


ambiguity

by deadlybride



Series: zmediaoutlet [6]
Category: Supernatural
Genre: Dean in Makeup, Established Relationship, Feminization, M/M, Panty Kink, Praise Kink, slight miscommunication
Language: English
Status: Completed
Published: 2016-12-05
Updated: 2016-12-05
Packaged: 2018-09-06 14:26:17
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,155
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8756095
Author URL: https://archiveofourown.org/users/deadlybride/pseuds/deadlybride
Summary: Sam has a fantasy that he's long wanted to see realized. Dean misunderstands, at first, but Sam sets him straight.





	

**Author's Note:**

  * For [bratfarrar](https://archiveofourown.org/users/bratfarrar/gifts).



> This can be read as a stand-alone; it can also be considered a far-future coda to the series "it started with the kinks," with a Dean who is more comfortable in his skin. Reader's choice. :)

When Sam was a freshman he took an English class in film analysis, a course that he’d read online would be maybe kind of hard, but a fun way to fill a gen ed requirement. They’d watched some German movie during the queer cinema portion of the class, something scratchy and pastel-tinted from the eighties, and Sam still remembers the essay he wrote _._ What he remembers more is the protagonist’s boyfriend, quick-tongued and strong, knife-sharp and soft, laying in a bed draped in pink satin. Pretty. A dozen years or more since he saw it and it’s stuck with him—one of those things he gets reminded of at unexpected times, the memory catching like silk against brick. It’s better than a lot of memories he’s got.

They’ve just wrapped up a pretty simple case of ghost possession in Chicago—dead cop using the living to kill minor offenders, gruesome but easy to figure out once they got the details—and now Dean has declared that they absolutely must have deep dish before they leave. It's when they’re walking down Belmont to the nearest Giordano’s that a storefront catches Sam’s eye, and he stops in his tracks for a second. It’s—not the same, not what was in the movie, but it makes the memory rise in him again. Silk and flowers, soft pretty colors. The sort of thing you might buy your wife, but Sam doesn’t have a wife, does he.

“Dude, what are you doing?” Dean says. He’s got his hands tucked into his jacket pockets against the chilly wind, his stubble heavy because they were going too hard to allow for time to shower and shave. “I’m starving, man, and you know it takes an hour to make a good pie.”

“Yeah,” Sam says, but he’s miles away, in his head. Dean frowns a little, comes back down the sidewalk towards him, and he’s all denim and leather, short spiked hair, and Sam knows he’s got a gun in his waistband and knives hidden in his boots, but he flicks his eyes back toward the display anyway, and this time Dean’s eyes follow his, and he watches the way Dean’s expression goes shocked, pretty eyes wide and his soft pink mouth dropping open before he catches himself and sends a sidelong look Sam’s way.

After a moment, Dean says, “Making a Christmas list, Sammy?” His voice is deeper than usual, a little rougher. Not saying no.

Sam takes in a deep breath. “I’m gonna stop in here for a minute,” he says. Dean’s eyes flicker to the window, back to Sam. “You go on ahead, get us a table. I’ll catch up.”

A couple of guys walk past them and Dean watches them go, little knot of a frown pulling at his brows, before he looks back up at the window, at the lingerie and robes draped over muscular mannequins. “Okay,” he says, finally. “But you take too long and I’m having them put pineapple on your half.”

Sam huffs a laugh, something tight uncoiling in his chest. It’s not a no. “Deal,” he says, and Dean nods and turns to head back down the street, and Sam has no compunctions about watching him go, watching the long strong lines of him, and just thinking about what they’re going to do is a melting warmth in the pit of his stomach. He doesn’t know how he’s supposed to wait until they get home.

 

 

Sam’s in the library, doing his best to read this old Norse account of shapeshifters, but he knows he’s not taking anything in. He rubs his hand over his mouth, checks his watch again. _Give me an hour_ , Dean had said, and Sam’s still got ten minutes left. He flips the old tome closed when he finds himself restlessly jogging his knee, reading the same paragraph over and over again, and he has to wipe his sweaty palms on his jeans. He doesn’t know why he’s nervous, but he is, and he gets up and pours two glasses of whiskey from the decanter on the sideboard—and then swallows his down immediately, so he has to refill it, and then he stands there, waiting. He’s trying not to imagine anything, but—

His phone buzzes, in his pocket. _Your room?_ it says, and just at that, the arousal that’s been threatening on and off since they got back from Chicago last night surges up and his dick’s halfway there, chubbed up in his jeans. He writes back, _see you there_. It feels stupid, but—god, who cares, and he picks up the glasses he’s poured and heads down the hallways under the bright lights, and he gets there first, which is—it’s better, somehow. He puts the whiskey down on his desk, heels off his boots. He has to drag his palms over his hips again, has to close his eyes, and then Dean says, “Hey.”

He turns around and— _fuck_. “Hey,” he says back, voice a little faint, and then all he can do is take it in. Dean’s leaning against the doorway in what he probably thinks is a sexy pose but it just looks… good. The kimono-style robe Sam picked is a deep plum purple, sprays of pink cherry blossoms scattered over the silk that trails almost to Dean's ankles, and Dean’s left it open so that it reveals his pale chest, his deceptively soft stomach, the faintest hint of hair that disappears into the cream-colored panties sitting low on his hips, soft and delicate and sheer enough that Sam can see the heavy dark shape of Dean’s dick through the fabric. He licks his lips, drags his eyes up so that he can meet Dean’s.

“Drink?” he says. Dean bites the inside of his cheek but comes into the room, picks up the whiskey glass—the silk robe shifting as he moves, deceptively modest as it swings forward to cover him up again. He takes a drink, his eyes lowered. This close Sam can see the eyeliner making the dark sweep of his eyelashes even prettier, sooty and imperfectly applied. When he takes the glass away there’s the faintest sticky imprint of barely-there pink lip gloss, and when he flicks his eyes back up to meet Sam’s they’re a shock of familiar green, the purple silk making him glow, and Sam reaches out and trails his fingers along Dean’s jaw—he shaved this morning, but there’s already the faint prickling drag of golden stubble coming in. Dean holds his eyes, runs the tip of his tongue over the trace of whiskey shining on his already glossy mouth, and Sam pulls him forward and tastes it for himself, kisses him wide open with smoky peat and sticky artificial watermelon on his tongue.

He crowds Dean back against the desk, uses his height like he usually doesn’t and bends Dean back a little, leaning down to lick into his mouth, slow and thorough. Dean clenches his hands into Sam’s shirt, spreads his legs when Sam nudges a knee between his thighs, and Sam could—god, he could rub off against him right here, he really could, but that’s not how he wants this to go. He pulls back, breathing hard, and Dean face is flushed pink where Sam’s holding it between his palms. His eyes shudder open after a few seconds and it’s a shock, again, the eyeliner making them mysterious as he looks up at Sam.

Sam runs his thumbs along Dean’s cheekbones and Dean’s lips part, and it’d be easy to lean in and take them again, but then Dean puts his hands flat on Sam’s chest and pushes him back, just an inch.

“Feeling a little overdressed here, Sammy,” he says, voice low. His fingers go to the buttons on Sam’s flannel, undoing them one at a time. Sam lets him, trails his hands down the sides of Dean’s neck, over his broad strong shoulders where they’re covered in plum silk and just the feel of Dean’s muscles working under the fabric makes Sam’s dick jump in his jeans. He lets his hands slip down, over the silky curves of his back down to his waist, gripping the familiar dip of it made softer by the rich fabric. When Dean gets Sam's flannel all the way open he slips his fingers under Sam's t-shirt, flicks his eyes up as he splays his hands over Sam's abs, and then he says, "Bed?" with his eyes heavy and spread-pupil dark, and—and, " _God_ , yes," Sam says, but then he slips his hands down under the generous swell of Dean's ass and lifts him up, quick so that Dean grunts out a _Jesus, what_ — He hitches his knees over Sam's hips but it's just two long steps to the bed, and Sam's careful, bears him down to the edge of the mattress and puts a hand behind his back so he goes down easy, and Dean's got an arm hooked behind his neck so that Sam's held close, so that Sam can watch his eyes go from startled to heavy-lidded again, so that Sam only has to lean in a few inches to lick the last of the gloss from his lower lip, but his mouth is pink and wet as it is, so there's no real difference.

When he pulls back Dean's breathing hard and Sam breaks his grip, shrugs off his flannel and hauls his t-shirt over his head, and Dean puts out a hand to draw him back but Sam takes it and goes down to his knees on the linoleum floor instead, says, "Just let me look at you," and Dean blinks, but lets him.

He's left his hair soft and ungelled and he's honey-pale in the lamplight. Dark-lined shock of his eyes, freckles just-visible, white even teeth dragging over his lower lip as he bites the pink swell of it, watching Sam look at him. Sam puts his hands on the collar of the robe, splays it open and spreads it so he can see—and, and—"You shaved," he says, on half a breath. Dean's legs bare and pale, paler without the familiar fuzz of hair, and Sam sits back on his heels, has to press his palm in against his dick when it lurches, because _fuck_ , he didn't expect that.

"You like?" Dean says, spreading his knees a little, and—yeah, god yes, he circles his hands around Dean's ankles and slides them up unfamiliar soft-silk skin.

There's a tiny patch at the turn of his right knee, tiny prickle of hair against Sam's thumb that he rubs over, and just that little imperfection has Sam's pulse jumping and he groans, says, "You missed a spot," just to tease, but when he looks up Dean's frowning, and he says, "Sorry," scratchy-voiced, and Sam's haze clears, a little.

"No," he says, and Dean's frown deepens, but—god, Sam's not coherent enough for this. He rubs his thumb over that little patch of stubble again and Dean shifts, his knee bumping up into Sam's palm, and Sam just—he hooks his other hand under Dean's knee and drags them open, drags him forward so that his legs are bracketing Sam's body. Dean almost drops, gets his hands behind him so he doesn't fall, but Sam's moving, already, bent in close so he can drag his lips over all that silky bare skin, over the heavy muscle in Dean's thigh that jumps when Sam licks over it. There's a tiny wound from the razor, right near where his thigh disappears into the soft cream panties and Sam kisses there, soft with just the tip of his tongue glancing over the cut, and Dean hitches in a breath over Sam's head, his hips shifting, and when Sam pulls back and looks—yeah, the panties aren't any kind of modesty, Dean's dick swelling up dark and obvious behind the sheer cream silk.

Sam slides his hands under Dean's thighs, spreads them wider and gets his palms over the soft perfect curve of his ass so he can lift his hips a little higher, so he can breathe hot against where Dean's dick is filling up the panties, his nose brushing the barely-there treasure trail. Dean hisses air in between his teeth and Sam presses a kiss over the crown of his dick and looks up and meets Dean's wide eyes, and says, "You know what I like?"

"What," Dean says, on half a breath.

Sam tips him onto his back, stands up and undoes his belt, his jeans, while Dean's splayed out and pretty, purple silk all over Sam's bed. "I really like sucking your dick," Sam says, shoving his jeans down, and it's nothing but honest but Dean squeezes his eyes shut, shivers.

Naked, finally, and his own dick bobs up eager and already wet at the tip and he's got to stroke himself, just once, because just Dean laying there flushed and willing is _killing_ him.

Dean's eyes fly open when Sam knees up onto bed, and Sam leans down and kisses him, once, full on the mouth, but then he grabs Dean by the waist and hauls him upright, falls onto his own back and pulls Dean into place over his hips, the kimono flaring out silkily over Sam's legs when Dean shifts his weight on his knees, settles into place with his ass plush against the tops of Sam's thighs, his throat flushed pink. Sam splays the robe open a little more, slips his fingers over the soft skin of Dean's ribs. "Know what else I like," he says, and Dean just blinks at him, and Sam hooks an arm around Dean's lower back and hitches him a little closer, leans up and covers one of Dean's nipples with his mouth, flicking his tongue over the soft of it until it buds up hard, the skin going tight. "Sam," Dean says, breathless, cupping the back of his head, and Sam grazes his teeth lightly over the tight point and switches to the other side, sucking hard when Dean groans, loud, and his hips kick into Sam's, crushing silk against Sam's dick. Dean's soft, here, his skin silky wet under Sam's tongue, and he's always had that plush layer to him but his pec is jumping under Sam's mouth, strong muscle revealing itself when it needs to, and—and Sam picks his head up, breathing hard, scrapes his teeth along Dean's tattoo and up to his flushed throat, licks there where the sweat is starting to shine and says, "You know what else I like?"

Deans got both hands buried in his hair now and he's breathing hard, his chest heaving under Sam's chin. "What?" he says, and it's soft, but it's raw, not putting on a show, and Sam drops a hand to that tiny patch of unshaved hair, slides from there up the silky back of his thigh, to where the panties start. He runs his fingers along them, along the tiny silk ruffles at the back that he'd almost combusted over, standing in that ridiculous store and imagining them on his brother, and he says, "I love your ass," almost under his breath, and Dean's hands tighten so hard in his hair that it hurts.

He takes Dean's ass in both hands, kneading deep, and that kicks Dean's hips forward again, grinds him up tight against where Sam's own dick is straining, desperate, but he gets himself together, says, "I could eat you out," and Dean groans, tucks his face down so Sam's talking against his ear, the plum-silk broad arch of his shoulder. "Or I could pull you open with my fingers, make a little room. I like both, you know." Dean shudders, says _Sammy, holy shit_ , up close into Sam's hair, and Sam shoves the panties down at the back, slides his fingers down and—

"You're wet," he says, and his voice comes out low and almost like a snarl and he didn't mean to, but it makes Dean shudder again, and Dean says tucked in close against him, so shivery-low it's almost hard for Sam to hear: "In the bag, you left lube in the bag, so I got myself ready, so you could just have me easy," and Sam grabs him by the jaw and pulls him up and kisses him, wide open and their teeth clashing, and Dean's still got both hands in his hair and so it's left up to Sam to yank the panties out of the way, to fumble his dick into place and push into soft slick heat and— _god,_ yeah, Dean moans out loud into Sam's mouth and maybe he didn't stretch himself as much as Sam would've but he clearly doesn't care, and then Sam's surrounded, in the slippery tight clutch of him, and he has to take a second because he could just blow right then, right there, die happy.

"Do you—" he starts, but Dean shifts against him and he cuts off with a groan, slips his hands up Dean's sides and pushes so that Dean's sitting upright, so that he can think. Dean tips his head back as Sam slips deeper, groans aloud at the ceiling, and he's—god, he's the hottest thing Sam's ever seen, the robe slipping off one shoulder and falling down so Sam can see the curve of tight muscle, the top of his heavy bicep. He swallows, tries to keep it together. "Do you know what else I like?"

Dean tips his head down, opens his eyes with what looks like an effort. His throat and chest are flushed dark, now, bright spots of color in his cheeks, and Sam licks his lips, slides his hands up Dean's silky bare thighs and says, "I like it when you get yourself off, on me, when you come on me," and Dean's eyes shock wide, but then Sam grabs his hands, steadies him, and Dean rocks up, lifts himself a little way off Sam's dick and sits back down again, and Sam groans but says, "Like that, yeah, go on," and then he's moving in earnest, loosening up around Sam's dick, chasing a rhythm for himself with his eyes closed and his hands planted flat on Sam's chest, keeping him still.

Sam keeps his eyes open, drinking it in, though he's got to do everything he can to keep from coming. Dean's got his teeth dug into his lower lip, sweat starting at his temples, his chest, dampening the silk when Sam runs a hand up his back to feel the way his muscles move as he bounces himself on Sam's dick. Sam shifts his hips a little, draws his knees higher, and when Dean comes down again he lets out a yelp, and—yeah, he's found it exactly, because he leans deep into it, drops his head down between his shoulders and lets his hips go slow, a swiveling grind that makes Sam bite his tongue, clench his thighs tight, doing all he can to hold back.

"Feel good?" he manages, and Dean nods but doesn't open his eyes, just shifts his hands to the mattress on either side of Sam's head, leaned in so Sam can see the way his expressions flicker, the sides of the kimono falling down around them and creating a little separate world. Sam slides his hands over Dean's chest, circles his still-damp nipples with his thumbs to see him flinch and then slips one hand down further, to cup his dick, his balls where they're trapped in the silk.

Dean moans, works his hips a little faster. "Don't—" he breathes, and Sam holds still, waiting, but Dean just slams down harder, so Sam doesn't move his hand, doesn't move his hips, just presses Dean's leaking dick up against his quivering stomach, cups his face in his other hand and moves his thumb over the parted plush of his mouth and feels Dean breathing against his skin, and it feels good, god, it feels really, really good, and when he thinks he's not going to be able take anymore Dean's breath hitches, he says, "Now, Sammy, I'm going to—" and Sam looks down into the space between their bodies and Dean grinds against him, hard, clenching deep and then he's—coming, yeah, pulsing and ruining the pretty cream panties Sam bought for him, spilling through the silk onto Sam's hand, his stomach. Sam drags his face down and smashes their mouths together, slings his other arm over Dean's sweaty silk-covered back and braces his feet against the bed and fucks up, finally, works his hips like he's been dying to for ages. Dean collapses down against him, breathes open and wet against Sam's mouth and he's still spasming, letting out little jolted-out moans every time Sam buries himself deep, and it's that, it's right there, and it's not a minute more before Sam crushes Dean against him and pulses his hips up so hard they're both lifted off the bed and comes, finally, his hips quivering against Dean's perfect ass for a long, long moment. Dean lifts up on one elbow, pushes back into him with a little _ah_ , and Sam opens his eyes—doesn't know when he closed them—and Dean's looking back at him, eyeliner a smeared-wet wreck, but then he tilts his head back down and kisses Sam, soft, little damp presses against the curve of Sam's mouth while Sam's hips twitch, dick working out the last of it, and Sam just breathes. It feels like his soul's been wrung out until he's been left clean, empty, warm.

It's some time much later that Dean sits up, groaning as he straightens his back out. The kimono drops further, catches around his elbows, and he lets out a sigh, rolling his head around on his neck until something pops.

"Okay?" Sam says, his breath barely settled.

Dean slits his eyes open, gives him a long look, but he doesn't say anything—instead he lifts himself off Sam's softening dick, grunts when it's out, and then tips over, to the side, so that Sam has to shuffle over to make enough room for them to lay together, Dean's thigh and a long tangle of purple silk caught over Sam's hips. When Sam looks, Dean's got an arm curled up under his head with his eyes closed, the robe still half-on, clinging to his cooling sweat.

"Thanks," Sam says, after a minute.

Dean sighs. "No big deal, Sammy," he says, and Sam rolls into him, lays a hand on his silk-covered hip and kisses the corner of his mouth, and Dean opens his eyes, reluctantly.

"What's the hottest thing you can think of?" Sam says. Dean frowns, and then his expression goes wicked, so Sam clarifies: "Something two people can do, which doesn't involve any animated tentacles."

Dean bites his lip. "Uh—I mean, you've got a pretty broad choice there, dude."

Sam snorts, props his head up on his hand. Dean rolls his head so he can keep looking at him, and Sam takes his other hand and runs his thumb carefully along the damp smear of eyeliner, cleans up the line of it. Dean blinks at him. "Well, we just managed the hottest thing I can think of," Sam says, and Dean's eyebrows go high, startled. Sam shrugs, one-sided. "So. Whatever you decide on, I'm game."

Dean glances down at himself, pulls the silk a little higher over his shoulder. "Good to know," he says, but his voice is too-deep and he has to clear his throat. When he looks up at Sam again his eyes are soft, his face open, and Sam wishes he were five years younger so they could go again, right this second. Dean bites his lip, brow furrowing. "You think they make cheerleader outfits in your size?"

Sam's mouth drops open. "What?"

Dean nods, seriously, but his eyes are starting to crinkle. "Yeah, I can see it now," he says, and Sam sits up over him, looking for the pillow to smack him with. "We'll get you one of those little ruffled skirts and some pom poms and one of those little college-girl sweaters, maybe some ribbons for your pigtails," and by the time Sam does get the pillow and hits him over the face with it Dean's laughing, full-out, but he's still with it enough to snatch the pillow out of Sam's hands and throw it out the open door into the hallway. He catches the back of Sam's neck with one hand, keeps him close.

"You want me to learn a little cheer, too?" Sam says, dry, but he gamely props himself up over Dean anyway.

"Yeah," Dean says, spreading his legs so Sam can settle between them. His eyes are bright, mouth relaxed into a grin. Sam can't help but smile back. "Yeah, Sammy, that'd be good."

 

**Author's Note:**

> [posted here on my tumblr if you'd like to reblog](http://zmediaoutlet.tumblr.com/post/154058569237/read-on-ao3-when-sam-was-a-freshman-he-took-an)


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